Diisopropylethylamine → HCID 52917353, compound

HRID 2172973Notes

Reaction equation

HRID 2172973 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[Br:20][C:21]1[CH:22]=[C:23]([C:27]2([NH2:30])[CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[Br:20][C:21]1[CH:22]=[C:23]([C:27]2([NH:30][C:17]([C:16]3[C:11]4[CH:10]=[N:9][N:8]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=5)[C:12]=4[CH:13]=[N:14][CH:15]=3)=[O:19])[CH2:28][CH2:29]2)[CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 111275641-(3-Bromophenyl)cyclopropanamineHCID 592781371-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid

Product 1

HCID 52917353HCID 52917353, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (0.500 g, 1.94 mmol), 1-(3-bromophenyl)cyclopropanamine (453 mg, 2.14 mmol) and N,N-diisopropylethylamine (1.73 mL, 9.72 mmol) in DMF (18 mL) is added TBTU (0.780 g, 2.43 mmol). After 2 hours, the mixture is concentrated in vacuo, dissolved in ethyl acetate (200 mL), and washed with 2N sodium hydroxide (3×100 mL), saturated aqueous ammonium chloride (2×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL). The organic layer is dried over MgSO4, filtered through a pad of silica gel eluting with ethyl acetate (3×100 mL), and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with a gradient of 50-70% ethyl acetate in heptane to give a solid that is triturated with methylene chloride to afford the title compound as a solid.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate (200 mL)
  3. washwashed with 2N sodium hydroxide (3×100 mL), saturated aqueous ammonium chloride (2×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered through a pad of silica gel eluting with ethyl acetate (3×100 mL)
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with a gradient of 50-70% ethyl acetate in heptane
  9. customto give a solid
  10. customthat is triturated with methylene chloride

Sources & evidence

ORD record
ord-3ffc21f2a46e46839c2ddfc2a323d2ec
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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